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Dimethyl Sulfate → Methyl 5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetate

HRID 370929
ノート
印刷プレビュー

反応式

HRID 370929 の反応式
Cl(O)(=O)(=O)=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=NC)[C:14]2[N:18]([CH3:19])[C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][C:15]=2[CH3:25])=[CH:9][CH:8]=1.C(=O)(O)[O-:29].[Na+].S(OC)(OC)(=O)=O.C([O-])(=O)C.[Na+]>CO.O>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:14]2[N:18]([CH3:19])[C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][C:15]=2[CH3:25])=[O:29])=[CH:9][CH:8]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6497Dimethyl SulfateHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 20275539HCID 20275539、化合物

生成物 1

HCID 618916Methyl 5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetate収率 65%

試薬・触媒・溶媒 2

HCID 887Methanol
溶媒
HCID 962Water溶媒2 回

実験手順

Methyl 5-[(4-chlorophenyl)(methylimino)methyl]-1,4-dimethyl-1H-pyrrole-2-acetate perchlorate (1.5 g, 3.6 mmole) was treated with saturated aqueous sodium bicarbonate and extracted with chloroform (50 ml). The organic phase was dried over magnesium sulfate, filtered and concentrated. The residue was treated with dimethyl sulfate (0.62 g, 4.9 mmole) and heated at ~40° C. for one hour. The viscous reaction mixture was dissolved in methanol (10 ml) and treated with sodium acetate (2 g, 24 mmole) and water (2 ml) and heated at reflux overnight. The reaction was cooled and diluted with water (5 ml). The crystalline solid was isolated by filtration, washed with water, air dried, and recrystallized from methanol (10 ml) to yield 0.71 g (65%) of the title compound as a tan solid, m.p. 125°-131° C.

後処理

  1. extractionextracted with chloroform (50 ml)
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. temperatureheated at ~40° C. for one hour
  6. temperatureheated
  7. temperatureat reflux overnight
  8. temperatureThe reaction was cooled
  9. customThe crystalline solid was isolated by filtration
  10. washwashed with water, air
  11. customdried
  12. customrecrystallized from methanol (10 ml)

出典と根拠

ORDレコード
ord-8a18e981360f43539173f7fbf808cea2
出典データセット
uspto-grants-1985_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04528382

反応ノート

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